Why Bennington VT Makes A Great Road Trip

Three hours and one bald eagle sighting from Boston by car, this artsy farm town offers a supercool overnight escape

A word of advice for fans of dead poets: Visit your idols no earlier than springtime. I learn this the hard way, trudging at sunset in deepest February across the frozen tundra of the Bennington Centre Cemetery, towards the gravesite of personal hero and New England literary icon, Robert Frost. The winding paths of hard-packed ice and arctic mud are treacherous—you would give better odds to a fugitive hamster crossing a busy freeway—but I finally reach Old Frosty (as I now call him) in a hot funk of nearly-cracked elbows and un-poetic expletives.

“I had a lover’s quarrel with the world,” reads Frost's epitaph. He must have seen me coming.

Robert Frost's grave in Vermont

This won’t be my only trek over two days in the quiet and utterly charming mountain town of Bennington, tucked into the very southwest corner of Vermont four miles from New York and 10 from Massachusetts. There’s much more to see here than Frost, especially in the full throes of spring.

Bennington presents an appealing mix of farmer and artisan, hippie and hipster.

Along historic Main Street (Route 9) and South Street (Route 7)—or North Street, depending on which side of Main Street you’re on—there is an enterprising mix of boutiques, cafes, restaurants and art galleries.

Fiddlehead at Four Corners is a funky art-space that demands hands-on interaction, whether it's drawing on the walls of a repurposed bank vault with chalk, playing a few notes of Louis Armstrong’s “What a Wonderful World” on the gallery’s piano or shooting a free game of pinball on a vintage machine. The current exhibit explores banned books of the 20th and 21st centuries, which is right up my alley.

Nearby at The Village Chocolate Shoppe, the lemon and olive oil notes laced in the handmade, 32-percent milk chocolate Il sapore del cioccolato bars recall lemon-scented days spent in Sorrento when I was 22. I stop in at South Street Cafe for an almond milk chai latte and catch a live, mid-afternoon acoustic set. Live, mid-afternoon acoustic sets are very Bennington.

Maker Culture

Maker culture here is huge here, extending from the town's signature potters to its craft brewers. On this quiet afternoon, I sidle up to the bar at veteran hop house Madison Brewing Co. as my first stop in an investigation of the local beer scene. It’s hard not to notice that this town loves beer. There’s a ‘tap room’ at every corner, although the term seems to have generalized to mean any bar with local beers on tap, not limited to those of its own making.

Bennington has started breeding craft brewers, too, and that’s why I’m at Madison sampling my way through eight of its signature drafts, including the super light Suckerpond Blonde, the orange-scented Wassicks Belgian White wheat and the malty English Yorkshire style Old 76 Strong Ale.

Madison Brewing Co. sampler in Vermont

Harvest Brewing is part bar, part co-op: Members use its 15-gallon brewing station and fermenting cellar to produce beer or cider, which Harvest then sells as part of its nanobrewery. Locals hang out here four nights per week to drink, play darts and pingpong, jam to live music or make their own at the frequent open mic nights.

Beer-making meets glass-making atop the corrugated metal bar at The Tap House at Catamount Glass where, later, I digest a fresh pint of Northshire Brewing Co.’s Equinox pilsner. The compact space is packed with midweek diners digging into homemade vegetable barley soup (served in Catamount glass bowls, of course) and Beyoncé Burger—they put an onion ring on it.

Perhaps the most widely recognized local maker is Bennington Potters. At 68 years young, this is not your Grandma’s stoneware pottery. The hand-thrown, glazed vessels nail that contemporary take on the basic Arts and Crafts aesthetic, and I am bringing a couple trigger mugs—imagine a vintage pistol trigger—home.

Diversion to Hoosick Falls

Statistics and user experience show that Vermont is an incredibly rural state, still today. Zipping along Route 9 aka the Molly Stark Trail, I head to get out of town for a few hours and investigate the surrounding countryside. Cows and sheep grazing on acres of patchwork fields; hay bales and grain silos; fresh farm eggs for sale; the occasional dilapidated barn: these timeless images flash past like slides in the View-Master I played with in the ‘80s.

After a few miles, I cross the state border into New York. The route number changes (to 7), but the landscape does not. After a few miles more, a herd of larger-than-life dairy cows and cow-spotted bears (?!) captures my attention on the roof of roadside attraction Big Moose Deli & Country Store. Obviously, I’ve got to pull over.

Marilyn Monroe, Batman and a hot dog slathering its own self in mustard welcome me through the door to a labyrinthine lair of kitsch that I clearly need to peruse. I’m talking “Special Shit” meat rubs, Hell’s Angel salt and pepper shakers, grass flip-flops, bacon-flavored soda, souvenir magnets and local jam.

Knickknack salt shaker on display Big Moose Deli & Country Store in Vermont

My brain is over-stimulated from this detour and my belly is famished, so on my way out I order the self-celebrated, ‘famous’ pulled pork sandwich, which weighs in at a pound of hickory-smoked pork slathered in house-made maple barbecue sauce and coleslaw from the food counter that’s nearly hidden behind the register. It is good.

Back behind the wheel and still licking barbecue sauce off my fingers, I turn up Route 22. It’s a quick ride north to Hoosick Falls, New York. The village center is listed as a historic district on the National Register, but today the former 19th century boomtown gives off a quiet, ghost-town vibe.

Nonetheless, there are two things to see here: Iron Coffee and Grandma Moses.

The former is the center’s only modern storefront and inside it smells like coffee and freshly cut wood. Coffee buffs can get a buzz on beans from Sumatra, Guatemala, Ethiopia and Brazil that are roasted in-house by the coffee house’s owner, who recommends his favorite (the Guatemala).

The latter is as much an icon of the region as she is in folk art circles. It’s in this valley where the artist spent her formative years and returned to later in life. It’s also the place where her paintings got noticed first. Visitors can view her grave at Maple Grove Cemetery (and the largest collection of her paintings in the world back in Bennington at the Bennington Museum).

Factory glass on display at the Bennington Museum in Vermont

Returning to Bennington from the west, the Bennington Battle Monument rises from the horizon like a solitary sentry on a battlefield. It recalls the single spire of the Strasbourg Cathedral de Notre Dame that Alsatians use as a beacon when navigating the flat landscape of their border region. Commemorating an important Revolutionary War battle, the state’s tallest structure resembles the Bunker Hill Monument in Boston, the Washington Monument on the National Mall in D.C., and, even, the Luxor Obelisk at Place de la Concorde in Paris.

A Classic and a Hidden Gem

Vermont is famous for its covered bridges, and it’s hard not to notice them while you’re on the road. Five are located within Bennington County, so I decide to head away from downtown on Route 67 to drive through the closest three. Mind the road, it’s one car at a time! These bridges over the Wallomsac River are as sturdy as they come, despite their 175 years.

Park-McCullough House in Vermont

I end up in North Bennington and drive past the Park-McCullough House to admire its opulent architecture—totally worth it—but I recommend bypassing an interior tour of this building to instead hike the Mile-Around Woods just beyond and behind the property. To reach the entrance to the hiking path, I have to park on the side of the road and tramp through someone’s horse field to the tune of train whistles and the rustling leaves of huge, old-wood oaks. Don’t bother feeling weird about trespassing. The well-worn path is evidence of frequent foot traffic.

Among the cows, the craft and the quiet, my thoughts return to Old Frosty's headstone. I think my quarrel’s been resolved.